The present invention relates to 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I 
where:
X is O, NR6 or CR7R8;
Y is O, S, NR9 or CR10R11;
R1 is nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfonyl or C1-C4-haloalkylsulfonyl;
R2,R3,R7,R8,R10,R11 are hydrogen, C1-C4-alkyl or C1-C4-haloalkyl;
or
R3 and R6 or R3 and R8 or R3 and R9 or R3 and R11 together form a bond;
R4 is halogen, nitro, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfonyl or C1-C4-haloalkylsulfonyl;
R5 is hydrogen, halogen or C1-C4-alkyl;
R6,R9 are hydrogen or C1-C6-alkyl;
R12 is hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C1-C6-alkylsulfonyloxy, C1-C6-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R13 is a cyclic ring system containing 3 to 14 ring atoms which may be partially or fully halogenated and/or may carry one to three of the following groups: C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl or C1-C4-haloalkoxy;
R14 is hydrogen or C1-C4-alkyl;
and their agriculturally useful salts.
Moreover, the invention relates to processes for preparing compounds of the formula I, to compositions comprising them and to the use of these derivatives or of compositions comprising them for controlling harmful plants.
Cycloalkyl-substituted pyrazolylbenzoyl derivatives which are substituted in the 3-position of the benzoyl radical by an N-bonded heterocycle or by phenyl are disclosed in the literature, for example in WO 98/42678 and WO 98/52926.
However, the herbicidal properties of the prior art compounds and their compatibility with crop plants may not be entirely satisfactory.
It is an object of the present invention to provide novel, in particular herbicidally active, compounds having improved properties.
We have found that this object is achieved by the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I and their herbicidal action.
Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal action. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.
Depending on the substitution pattern, the compounds of the formula I may contain one or more chiral centers, in which case they are present as enantiomers or mixtures of diastereomers. The invention provides both the pure enantiomers or diastereomers and their mixtures.
The compounds of the formula I can also be present in the form of their agriculturally useful salts, the kind of salt usually being immaterial. In general, the salts of those cations or the acid addition salts of those acids are suitable whose cations and anions, respectively, do not adversely affect the herbicidal action of the compounds I.
Suitable cations are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium, where, if desired, one to four hydrogen atoms may be replaced here by C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl, preferably ammonium, dimethylassonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
The organic molecular moieties mentioned for the substituents R1-R12 or as radicals on phenyl rings are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, i.e. all alkyl, alkylcarbonyl, haloalkyl, alkoxy, haloalkoxy, alkylcarbonyloxy, alkylsulfonyloxy, alkylthio, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, alkenyl and alkenyloxy moieties can be straight-chain or branched. Unless indicated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. The term halogen represents in each case fluorine, chlorine, bromine or iodine.
Examples of other meanings are:
C1-C4-alkyl, and the alkyl moieties of C1-C4-alkylcarbonyl and C1-C4-alkylcarbonyloxy: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;
C1-C6-alkyl, and the alkyl moieties of C1-C6-alkylcarbonyl and C1-C6-alkylcarbonyloxy: C1-C4-alkyl as mentioned above, and also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl;
C1-C4-haloalkyl: a C1-C4-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoramethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromoethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl;
C1-C4-alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;
C1-C6-alkoxy: C1-C4-alkoxy as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;
C1-C4-haloalkoxy: a C1-C4-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy;
C1-C4-alkylthio: for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio;
C1-C4-haloalkylthio: a C1-C4-alkylthio radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio and nonafluorobutylthio;
C1-C4-alkylsulfonyl (C1-C4-alkyl-S(xe2x95x90O)2-), and the alkylsulfonyl moieties of C1-C4-alkylsulfonyloxy: for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl and 1,1-dimethylethylsulfonyl;
C1-C6-alkylsulfonyl, and the alkylsulfonyl moieties of C1-C6-alkylsulfonyloxy: a C1-C4-alkylsulfonyl radical as mentioned above, and also, for example, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl;
C1-C4-haloalkylsulfonyl: a C1-C4-alkylsulfonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl, 1-(chloromethyl)-2-chloroethylsulfonyl, 1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl and nonafluorobutylsulfonyl;
C3-C6-alkenyloxy: for example prop-1-en-1-yloxy, prop-2-en-1-yloxy, 1-methylethenyloxy, buten-1-yloxy, buten-2-yloxy, buten-3-yloxy, 1-methylprop-1-en-1-yloxy, 2-methylprop-1-en-1-yloxy, 1-methylprop-2-en-1-yloxy, 2-methylprop-2-en-1-yloxy, penten-1-yloxy, penten-2-yloxy, penten-3-yloxy, penten-4-yloxy, 1-methylbut-1-en-1-yloxy, 2-methylbut-1-en-1-yloxy, 3-methylbut-1-en-1-yloxy, 1-methylbut-2-en-1-yloxy, 2-methylbut-2-en-1-yloxy, 3-methylbut-2-en-1-yloxy, 1-methylbut-3-en-1-yloxy, 2-methylbut-3-en-1-yloxy, 3-methylbut-3-en-1-yloxy, 1,1-dimethylprop-2-en-1-yloxy, 1,2-dimethylprop-1-en-1-yloxy, 1,2-dimethylprop-2-en-1-yloxy, 1-ethylprop-1-en-2-yloxy, 1-ethylprop-2-en-1-yloxy, hex-1-en-1-yloxy, hex-2-en-1-yloxy, hex-3-en-1-yloxy, hex-4-en-1-yloxy, hex-5-en-1-yloxy, 1-methylpent-1-en-1-yloxy, 2-methylpent-1-en-1-yloxy, 3-methylpent-1-en-1-yloxy, 4-methylpent-1-en-1-yloxy, 1-methylpent-2-en-1-yloxy, 2-methylpent-2-en-1-yloxy, 3-methylpent-2-en-1-yloxy, 4-methylpent-2-en-1-yloxy, 1-methylpent-3-en-1-yloxy, 2-methylpent-3-en-1-yloxy, 3-methylpent-3-en-1-yloxy, 4-methylpent-3-en-1-yloxy, 1-methylpent-4-en-1-yloxy, 2-methylpent-4-en-1-yloxy, 3-methylpent-4-en-1-yloxy, 4-methylpent-4-en-1-yloxy, 1,1-dimethylbut-2-en-1-yloxy, 1,1-dimethylbut-3-en-1-yloxy, 1,2-dimethylbut-1-en-1-yloxy, 1,2-dimethylbut-2-en-1-yloxy, 1,2-dimethylbut-3-en-1-yloxy, 1,3-dimethylbut-1-en-1-yloxy, 1,3-dimethylbut-2-en-1-yloxy, 1,3-dimethylbut-3-en-1-yloxy, 2,2-dimethylbut-3-en-1-yloxy, 2,3-dimethylbut-1-en-1-yloxy, 2,3-dimethylbut-2-en-1-yloxy, 2,3-dimethylbut-3-en-1-yloxy, 3,3-dimethylbut-1-en-1-yloxy, 3,3-dimethylbut-2-en-1-yloxy, 1-ethylbut-1-en-1-yloxy, 1-ethylbut-2-en-1-yloxy, 1-ethylbut-3-en-1-yloxy, 2-ethylbut-1-en-1-yloxy, 2-ethylbut-2-en-1-yloxy, 2-ethylbut-3-en-1-yloxy, 1,1,2-trimethylprop-2-en-1-yloxy; 1-ethyl-1-methylprop-2-en-1-yloxy, 1-ethyl-2-methylprop-1-en-1-yloxy and 1-ethyl-2-methylprop-2-en-1-yloxy;
C3-C6-alkenyl: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, hex-1-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-yl and 1-ethyl-2-methylprop-2-en-1-yl.
The term xe2x80x9ccyclic ring system having 3 to 14 ring atomsxe2x80x9d denotes: C3-C8-cycloalkyl, C3-C8-cycloalkenyl, a bi- or tricyclic carbocyclic or heterocyclic ring system having up to 14 ring atoms, where the ring system may be saturated or contain one, two or three double bonds and, in the case of the heterocyclic rings, may contain one to three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur. The xe2x80x9ccyclic ring systems having 3 to 14 ring atomsxe2x80x9d may be partially or fully halogenated and/or may carry one to three of the following groups:
C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl or C1-C4-haloalkoxy.
Examples of other meanings are:
C3-C6-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
C3-C8-cycloalkyl: C3-C6-cycloalkyl as mentioned above, and also cycloheptyl or cyclooctyl;
C5-C6-cycloalkenyl: cyclopentenyl or cyclohexenyl;
C3-C6-cycloalkenyl: C5-C6-cycloalkenyl as mentioned above, and also cyclopropenyl or cyclobutenyl;
C3-C8-cycloalkenyl: C3-C6-cycloalkenyl as mentioned above, and also cycloheptenyl or cyclooctenyl;
bi- or tricyclic ring system: for example adamantyl, norbornyl, camphyl, camphenyl or norbornenyl.
The phenyl rings are preferably unsubstituted or carry one to three halogen atoms and/or one nitro group, one cyano group, one or two methyl, trifluoromethyl, methoxy or trifluoromethoxy groups.
Emphasis is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where the variables both on their own and in combination with one another have the following meanings:
X is O, NR6 or CR7R8;
Y is O, S, NR9 or CR10R11;
R1 is nitro, halogen, C1-C4-alkyl or C1-C4-alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, C1-C4-alkyl, such as methyl or ethyl, or C1-C4-alkoxy, such as methoxy or ethoxy; with very particular preference chlorine, methyl or methoxy;
R2,R3,R7,R8,R10,R11 are hydrogen, C1-C4-alkyl or C1-C4-haloalkyl; particularly preferably hydrogen, methyl, ethyl, propyl, 1-methylethyl, fluoromethyl or chloromethyl; with very particular preference hydrogen, methyl, ethyl or chloromethyl;
or
R3 and R6 or R3 and R8 or R3 and R9 or R3 and R11 together form a bond;
R4 is halogen, nitro, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-alkylsulfonyl; particularly preferably halogen, such as chlorine or bromine, nitro, C1-C2-haloalkyl, such as difluoromethyl or trifluoromethyl, C1-C2-alkoxy, such as methoxy or ethoxy, C1-C2-haloalkoxy, such as difluoromethoxy, chlorodifluoromethoxy or trifluoromethoxy, C1-C3-alkylthio, such as methylthio, ethylthio or 1-methyl-1-ethylthio, or C1-C3-alkylsulfonyl, such as methylsulfonyl, ethylsulfonyl, 1-methylethylsulfonyl or propylsulfonyl;
R5 is hydrogen, halogen or methyl or ethyl; particularly preferably hydrogen, chlorine or methyl; with very particular preference hydrogen;
R6, R9 are hydrogen or C1-C4-alkyl; particularly preferably hydrogen, methyl or ethyl; with very particular preference methyl;
R12 is hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C1-C6-alkylsulfonyloxy, C1-C6-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; particularly preferably hydroxyl, C1-C4-alkoxy, C3-C6-alkenyloxy, C1-C4-alkylsulfonyloxy, C1-C4-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R13 is C3-C8-cycloalkyl, C3-C8-cycloalkenyl, a bi- or tricyclic carbocyclic or heterocyclic ring system having up to 14 ring atoms, where the ring system may be saturated or contain one, two or three double bonds and, in the case of the heterocyclic rings, may contain one to three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur. The xe2x80x9ccyclic ring systems having 3 to 14 ring atomsxe2x80x9d may be partially or fully halogenated and/or may carry one to three of the following groups: C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl or C1-C4-haloalkoxy;
particularly preferably C3-C8-cycloalkyl, C3-C8-cycloalkenyl or a bi- or tricyclic carbocyclic ring system which contains up to 14 ring atoms and is saturated or contains one, two or three double bonds, and where the radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups: C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl or C1-C4-haloalkoxy; with very particular preference C3-C6-cycloalkyl, C5-C6-cycloalkenyl or a bi- or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl or norbornenyl; more preferably C3-C6-cycloalkyl; with most preference cyclopropyl;
R14 is hydrogen or C1-C4-alkyl; particularly preferably hydrogen or methyl.
Preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where:
X is O;
R1 is nitro, halogen, C1-C4-alkyl or C1-C4-alkoxy; particularly preferably halogen, C1-C4-alkyl or C1-C4-alkoxy; with particular preference halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with very particular preference chlorine, methyl or methoxy;
R4 is halogen, nitro, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-alkylsulfonyl; particularly preferably halogen, such as chlorine or bromine, nitro, C1-C2-haloalkyl, such as difluoromethyl or trifluoromethyl, C1-C2-alkoxy, C1-C2-haloalkoxy, such as difluoromethoxy, chlorodifluoromethoxy or trifluoromethoxy, C1-C2-alkylthio, such as methylthio or ethylthio, or C1-C2-alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl.
Particular preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is O;
Y is CR10R11;
R1 is halogen, C1-C4-alkyl or C1-C4-alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with very particular preference chlorine, methyl or methoxy;
R2,R3,R10,R11 are hydrogen, C1-C4-alkyl; or R3 and R11 together form a bond; particularly preferably hydrogen, methyl or ethyl; or R3 and R11 together form a bond;
R4 is nitro, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; particularly preferably nitro, C1-C2-haloalkyl, such as difluoromethyl or trifluoromethyl, C1-C2-alkoxy or C1-C2-haloalkoxy, such as difluoromethoxy;
R5 is hydrogen;
R12 is hydroxyl, C1-C6-alkylsulfonyloxy, C1-C6-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; particularly preferably hydroxyl;
R13 is C3-C6-cycloalkyl, C5-C6-cycloalkenyl or a bi- or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C3-C6-cycloalkyl; with very particular preference cyclopropyl.
Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is O;
Y is CR10R11;
R2,R3,R10,R11 are hydrogen or methyl or ethyl; preferably hydrogen or methyl.
Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is O;
Y is CR10R11;
R2,R10 are hydrogen or methyl or ethyl; preferably hydrogen or methyl;
R3 and R11 together form a bond.
Particular preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is O;
Y is CR10R11;
R1 is halogen, C1-C4-alkyl or C1-C4-alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;
R2,R3,R10,R11 are hydrogen or C1-C4-alkyl; or R3 and R11 together form a bond; particularly preferably hydrogen, methyl or ethyl; or R3 and R11 together form a bond;
R4 is halogen, C1-C4-alkylthio or C1-C4-alkylsulfonyl; particularly preferably chlorine or bromine, methylthio, ethylthio or 1-methyl-1-ethylthio or methylsulfonyl, ethylsulfonyl, 1-methylethylsulfonyl or propylsulfonyl;
R5 is hydrogen;
R12 is hydroxyl, C1-C6-alkylsulfonyloxy, C1-C6-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; particularly preferably hydroxyl;
R13 is C3-C6-cycloalkyl, C5-C6-cycloalkenyl or a bi- or tricyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C3-C6-cycloalkyl; with particular preference cyclopropyl.
Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is O;
Y is CR10R11;
R2,R3,R10,R11 are hydrogen or methyl or ethyl; preferably hydrogen or methyl.
Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is O;
Y is CR10R11;
R2,R10 are hydrogen or methyl or ethyl; preferably hydrogen or methyl;
R3 and R11 together form a bond.
Preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where the variables have the following meanings:
X is NR6;
R1 is nitro, halogen, C1-C4-alkyl or C1-C4-alkoxy; particularly preferably halogen, C1-C4-alkyl or C1-C4-alkoxy; with particular preference halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with very particular preference chlorine, methyl or methoxy;
R4 is halogen, nitro, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-alkylsulfonyl; particularly preferably halogen, such as chlorine or bromine, nitro, C1-C2-haloalkyl, such as difluoromethyl or trifluoromethyl, C1-C2-alkoxy, such as methoxy or ethoxy, C1-C2-haloalkoxy, such as difluoromethoxy, chlorodifluoromethoxy or trifluoromethoxy, C1-C2-alkylthio, such as methylthio or ethylthio, or C1-C2-alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl.
Particular preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is N(C1-C6-alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;
Y is NR9 or CR10R11;
R1 is halogen, C1-C4-alkyl or C1-C4-alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;
R2,R3,R10,R11 are hydrogen or C1-C4-alkyl; or R3 and R9 or R3 and R11 together form a bond; particularly preferably hydrogen, methyl or ethyl; or R3 and R9 or R3 and R11 together form a bond;
R4 is nitro, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; particularly preferably nitro, C1-C2-haloalkyl, such as difluoromethyl or trifluoromethyl, C1-C2-alkoxy or C1-C2-haloalkoxy, such as difluoromethoxy;
R5 is hydrogen;
R9 is hydrogen or C1-C4-alkyl; particularly preferably C1-C4-alkyl; with particular preference methyl or ethyl;
R12 is hydroxyl, C1-C6-alkylsulfonyloxy, C1-C6-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; particularly preferably hydroxyl;
R13 is C3-C6-cycloalkyl, C5-C6-cycloalkenyl or a bi- or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C3-C6-cycloalkyl; with particular preference cyclopropyl.
Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is N-(C1-C6-alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;
Y is CR10R11;
R2,R3,R10,R11 are hydrogen or C1-C4-alkyl; preferably hydrogen, methyl or ethyl; particularly preferably hydrogen or methyl.
Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is N-(C1-C6-alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;
Y is NR9 or CR10R11;
R2,R10 are hydrogen or C1-C4-alkyl; preferably hydrogen, methyl or ethyl; with particular preference hydrogen or methyl;
R3 and R9 or R3 and R11 together form a bond.
Particular preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is N-(C1-C6-alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;
Y is NR9 or CR10R11;
R1 is halogen, C1-C4-alkyl or C1-C4-alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;
R2,R3,R10,R11 are hydrogen or C1-C4-alkyl; or R3 and R9 or R3 and R11 together form a bond; particularly preferably hydrogen, methyl or ethyl; or R3 and R9 or R3 and R11 together form a bond;
R4 is halogen, C1-C4-alkylthio or C1-C4-alkylsulfonyl; particularly preferably chlorine or bromine, methylthio, ethylthio or 1-methyl-1-ethylthio or methylsulfonyl, ethylsulfonyl, 1-methylethylsulfonyl or propylsulfonyl;
R5 is hydrogen;
R9 is hydrogen or C1-C4-alkyl; particularly preferably C1-C4-alkyl; with particular preference methyl or ethyl;
R12 is hydroxyl, C1-C6-alkylsulfonyloxy, C1-C6-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; particularly preferably hydroxyl;
R13 is C3-C6-cycloalkyl, C5-C6-cycloalkenyl or a bi- or tricyclic carbocyclic ring system, selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C1-C6-cycloalkyl; with particular preference cyclopropyl.
Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is N-(C1-C6-alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;
Y is CR10R11;
R2,R3,R10,R11 are hydrogen or C1-C4-alkyl; preferably hydrogen, methyl or ethyl; with particular preference hydrogen or methyl.
Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is N-(C1-C6-alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;
Y is NR9 or CR10R11;
R2,R10 are hydrogen or C1-C4-alkyl; preferably hydrogen, methyl or ethyl; with particular preference hydrogen or methyl;
R3 and R9 or R3 and R11 together form a bond.
Particular preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is NR6;
Y is O, S or N-(C1-C6-alkyl); particularly preferably O, S or N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;
R1 is halogen, C1-C4-alkyl or C1-C4-alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;
R2 is hydrogen or C1-C4-alkyl; particularly preferably hydrogen, methyl or ethyl;
R3 and R6 together form a bond;
R5 is hydrogen;
R12 is hydroxyl, C1-C6-alkylsulfonyloxy, C1-C6-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; particularly preferably hydroxyl;
R13 is C3-C6-cycloalkyl, C5-C6-cycloalkenyl or a bi- or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C3-C6-cycloalkyl; with particular preference cyclopropyl.
Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
R4 is nitro, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; particularly preferably nitro, C1-C2-haloalkyl, such as difluoromethyl or trifluoromethyl, C1-C2-alkoxy or C1-C2-haloalkoxy, such as difluoromethoxy.
Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
R4 is halogen, C1-C4-alkylthio or C1-C4-alkylsulfonyl; particularly preferably chlorine or bromine, methylthio, ethylthio or 1-methyl-1-ethylthio or methylsulfonyl, ethylsulfonyl, 1-methylethylsulfonyl or propylsulfonyl.
Preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where:
X is CR7R8;
R1 is nitro, halogen, C1-C4-alkyl or C1-C4-alkoxy; particularly preferably halogen, C1-C4-alkyl or C1-C4-alkoxy; with particular preference halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with very particular preference chlorine, methyl or methoxy;
R4 is halogen, nitro, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-alkylsulfonyl; particularly preferably halogen, such as chlorine or bromine, nitro, C1-C2-haloalkyl, such as difluoromethyl or trifluoromethyl, C1-C2-alkoxy, such as methoxy or ethoxy, C1-C2-haloalkoxy, such as difluoromethoxy, chlorodifluoromethoxy or trifluoromethoxy, C1-C2-alkylthio, such as methylthio or ethylthio, or C1-C2-alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl.
Particular preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is CR7R8;
Y is O, S or NR9;
R1 is halogen, C1-C4-alkyl or C1-C4-alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl, methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;
R2,R3,R7,R8 are hydrogen or C1-C4-alkyl; or R3 and R8 together form a bond; particularly preferably hydrogen, methyl or ethyl; or R3 and R8 together form a bond;
R4 is nitro, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; particularly preferably nitro, C1-C2-haloalkyl, such as difluoromethyl or trifluoromethyl, C1-C2-alkoxy or C1-C2-haloalkoxy, such as difluoromethyloxy;
R5 is hydrogen;
R9 is hydrogen or C1-C4-alkyl; particularly preferably C1-C4-alkyl;
R12 is hydroxyl, C1-C6-alkylsulfonyloxy, C1-C6-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; particularly preferably hydroxyl;
R13 is C3-C6-cycloalkyl, C5-C6-cycloalkenyl or a bi or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C3-C6-cycloalkyl; with particular preference cyclopropyl.
Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is CR7R8;
Y is O, S or NR9;
R2,R3,R7,R8 are hydrogen or C1-C4-alkyl; preferably hydrogen, methyl or ethyl; particularly preferably hydrogen or methyl;
R9 is hydrogen or C1-C4-alkyl; preferably C1-C4-alkyl.
Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is CR7R8;
Y is O, S or NR9;
R2,R7 are hydrogen or C1-C4-alkyl; preferably hydrogen, methyl or ethyl; particularly preferably hydrogen or methyl;
R3 and R8 together form a bond;
R9 is hydrogen or C1-C4-alkyl; preferably C1-C4-alkyl.
Especially preferred in this case are the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where Y is S.
Particular preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is CR7R8;
Y is O, S or NR9;
R1 is halogen, C1-C4-alkyl or C1-C4-alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;
R2,R3,R7,R8 are hydrogen or C1-C4-alkyl; or R3 and R8 together form a bond; particularly preferably hydrogen, methyl or ethyl; or R3 and R8 together form a bond;
R4 is halogen, C1-C4-alkylthio or C1-C4-alkylsulfonyl; particularly preferably chlorine or bromine, methylthio, ethylthio or 1-methyl-1-ethylthio or methylsulfonyl, ethylsulfonyl, 1-methylethylsulfonyl or propylsulfonyl;
R5 is hydrogen;
R9 is hydrogen or C1-C4-alkyl; particularly preferably C1-C4-alkyl; with particular preference methyl or ethyl;
R12 is hydroxyl, C1-C6-alkylsulfonyloxy, C1-C6-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; particularly preferably hydroxyl;
R13 is C3-C6-cycloalkyl, C5-C6-cycloalkenyl or a bi- or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C3-C6-cycloalkyl; with particular preference cyclopropyl.
Preference is furthermore given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is CR7R8;
Y is O, S or NR9;
R2,R3,R7,R8 are hydrogen or C1-C4-alkyl; preferably hydrogen, methyl or ethyl; particularly preferably hydrogen or methyl;
R9 is hydrogen or C1-C4-alkyl; preferably C1-C4-alkyl.
Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where
X is CR7R8;
Y is O, S or NR9;
R2,R7 are hydrogen or C1-C4-alkyl; preferably hydrogen, methyl or ethyl; with particular preference hydrogen or methyl;
R3 and R8 together form a bond;
R9 is hydrogen or C1-C4-alkyl; preferably C1-C4-alkyl.
Especially preferred in this case are the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where Y is S.
Preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where the variables have the following meanings:
X is O;
Y is CR10R11;
R1 is halogen, C1-C4-alkyl or C1-C4-alkoxy; particularly preferably chlorine, methyl or methoxy; also particularly preferably halogen or C1-C4-alkyl; with particular preference chlorine or methyl;
R1,R3,R10,R11 are hydrogen;
R4 is C1-C4-alkylsulfonyl; particularly preferably methylsulfonyl;
R5 is hydrogen;
R12 is hydroxyl, C1-C6-alkoxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; particularly preferably hydroxyl, C1-C6-alkoxy or phenylcarbonyloxy, where the phenyl radical may be partially or fully halogenated and/or may carry one to three of the following groups; nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R13 is C3-C6-cycloalkyl or a bi- or tricyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl or norbornenyl; particularly preferably cyclopropyl, cyclopentyl, 2-norbornyl or 2-adamantyl; with particular preference cyclopentyl or 2-norbornyl; also with particular preference cyclopropyl;
R14 is hydrogen;
Preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where the variables have the following meanings:
X is O;
Y is CR10R11;
R1 is halogen, C1-C4-alkyl or C1-C4-alkoxy;
R4 is C1-C4-alkylsulfonyl;
R13 is C3-C6-cycloalkyl.
Most particularly preferred are the compounds of the formula Ia1 (=I where R1=Cl; R13=cyclo-C3H5 and R5 and R14=H), in particular the compounds Ia1.1 to Ta1.765 of Table 1, where the radical definitions X, Y and R1 to R14 are of particular importance for the compounds according to the invention not only in combination with one another but also in each case on their own. 
Most particular preference is also given to the compounds of the formula Ia2, in particular to the compounds Ia2.1, to Ia2.765 which differ from the corresponding compounds Ia1.1 to Ia1.765 in that R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ia3, in particular to the compounds Ia3.1 to Ia3.765 which differ from the compounds Ia1.1 to Ia1.765 in that R13 is cyclopentyl. 
Most particular preference is also given to the compounds of the formula Ia4, in particular to the compounds Ia4.1 to Ia4.765 which differ from the compounds Ia1.1 to Ia1.765 in that R13 is cyclopentyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ia5, in particular to the compounds Ia5.1 to Ia5.765 which differ from the compounds Ia1.1 to Ia1.765 in that R13 is cyclohexyl. 
Most particular preference is also given to the compounds of the formula Ia6, in particular to the compounds Ia6.1 to Ia6.765 which differ from the compounds Ia1.1 to Ia1.765 in that R13 is cyclohexyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ia7, in particular to the compounds Ia7.1 to Ia7.765 which differ from the compounds Ia1.1 to Ia1.765 in that R13 is 2-norbornyl. 
Most particular preference is also given to the compounds of the formula Ia8, in particular to the compounds Ia8.1 to Ia8.765 which differ from the compounds Ia1.1 to Ia1.765 in that R13 is 2-norbornyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ia9, in particular to the compounds Ia9.1 to Ia9.765 which differ from the compounds Ia1.1 to Ia1.765 in that R13 is 2-adamantyl. 
Most particular preference is also given to the compounds of the formula Ia10, in particular to the compounds Ia10.1 to Ia10.765 which differ from the compounds Ia1.1 to Ia1.765 in that R13 is 2-adamantyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ia11, in particular to the compounds Ia11.1 to Ia11.765 which differ from the corresponding compounds Ia1.1 to Ia1.765 in that R1 is methyl. 
Most particular preference is also given to the compounds of the formula Ia12, in particular to the compounds Ia12.1 to Ia12.765 which differ from the corresponding compounds Ia1.1 to Ia1.765 in that R1 is methyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ia13, in particular to the compounds Ia13.1 to Ia13.765 which differ from the compounds Ia1.1 to Ia1.765 in that R1 is methyl and R13 is cyclopentyl. 
Most particular preference is also given to the compounds of the formula Ia14, in particular to the compounds Ia14.1 to Ia14.765 which differ from the compounds Ia1.1 to Ia1.765 in that R1 is methyl, R13 is cyclopentyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ia15, in particular to the compounds Ia15.1 to Ia15.765 which differ from the compounds Ia1.1 to Ia1.765 in that R1 is methyl and R13 is cyclohexyl. 
Most particular preference is also given to the compounds of the formula Ia16, in particular to the compounds Ia16.1 to Ia16.765 which differ from the compounds Ia1.1 to Ia1.765 in that R1 is methyl, R13 is cyclohexyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ia17, in particular to the compounds Ia17.1 to Ia17.765 which differ from the compounds Ia1.1 to Ia1.765 in that R1 is methyl and R13 is 2-norbornyl. 
Most particular preference is also given to the compounds of the formula Ia18, in particular to the compounds Ia18.1 to Ia18.765 which differ from the compounds Ia1.1 to Ia1.765 in that R1 is methyl, R12 is 2-norbornyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ia19, in particular to the compounds Ia19.1 to Ia19.765 which differ from the compounds Ia1.1 to Ia1.765 in that R1 is methyl and R13 is 2-adamantyl. 
Most particular preference is also given to the compounds of the formula Ia20, in particular to the compounds Ia20.1 to Ia20.765 which differ from the compounds Ia1.1 to Ia1.765 in that R1 is methyl, R13 is 2-adamantyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ia21, in particular to the compounds Ia21.1 to Ia21.765 which differ from the corresponding compounds Ia1.1 to Ia1.765 in that R1 is methoxy. 
Most particular preference is also given to the compounds of the formula Ia22, in particular to the compounds Ia22.1 to Ia22.765 which differ from the corresponding compounds Ia1.1 to Ia1.765 in that R1 is methoxy and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ia23, in particular to the compounds Ia23.1 to Ia23.765 which differ from the compounds Ia1.1 to Ia1.765 in that R1 is methoxy and R13 is cyclopentyl. 
Most particuiar preference is also given to the compounds of the formula Ia24, in particular to the compounds Ia24.1 to Ia24.765 which differ from the compounds Ia1.1 to Ia1.765 in that R1 is methoxy, R13 is cyclopentyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ia25, in particular to the compounds Ia25.1 to Ia25.765 which differ from the compounds Ia1.1 to Ia1.765 in that R1 is methoxy and R13 is cyclohexyl. 
Most particular preference is also given to the compounds of the formula Ia26, in particular to the compounds Ia26.1 to Ia26.765 which differ from the compounds Ia1.1 to Ia1.765 in that R1 is methoxy, R13 is cyclohexyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ia27, in particular to the compounds Ia27.1 to Ia27.765 which differ from the compounds Ia1.1 to Ia1.765 in that R1 is methoxy and R13 is 2-norbornyl. 
Most particular preference is also given to the compounds of the formula Ia28, in particular to the compounds Ia28.1 to Ia28.765 which differ from the compounds Ia1.1 to Ia1.765 in that R1 is methoxy, R13 is norbornyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ia29, in particular to the compounds Ia29.1 to Ia29.765 which differ from the compounds Ia1.1 to Ia1.765 in that R1 is methoxy and R13 is 2-adamantyl. 
Most particular preference is also given to the compounds of the formula Ia30, in particular to the compounds Ia30.1 to Ia30.765 which differ from the compounds Ia1.1 to Ia1.765 in that R1 is methoxy, R13 is 2-adamantyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ib1 (=I where R1=Cl, R3 and R9 or R3 and R11 together form a bond, R13=cyclo-C3H5 and R5 and R14=H), in particular to the compounds Ib1.1 to Ib1.420 of Table 2 where the radical definitions X, Y and R1 to R14 are of particular importance for the compounds according to the invention not only in combination with one another but also in each case on their own. 
Most particular preference is also given to the compounds of the formula Ib2, in particular to the compounds Ib2.1 to Ib2.420 which differ from the corresponding compounds Ib1.1 to Ib1.420 in that R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ib3, in particular to the compounds Ib3.1 to Ib3.420 which differ from the compounds Ib1.1 to Ib1.420 in that R13 is cyclopentyl. 
Most particular preference is also given to the compounds of the formula Ib4, in particular to the compounds Ib4.1 to Ib4.420 which differ from the compounds Ib1.1 to Ib1.420 in that R13 is cyclopentyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ib5, in particular to the compounds Ib5.1 to Ib5.420 which differ from the compounds Ib1.1 to Ib1.420 in that R13 is cyclohexyl. 
Most particular preference is also given to the compounds of the formula Ib6, in particular to the compounds Ib6.1 to Ib6.420 which differ from the compounds Ib1.1 to Ib1.420 in that R13 is cyclohexyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ib7, in particular to the compounds Ib7.1 to Ib7.420 which differ from the compounds Ib1.1 to Ib1.420 in that R13 is 2-norbornyl. 
Most particular preference is also given to the compounds of the formula Ib8, in particular to the compounds Ib8.1 to Ib8.420 which differ from the compounds Ib1.1 to Ib1.420 in that R13 is 2-norbornyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ib9, in particular to the compounds Ib9.1 to Ib9.420 which differ from the compounds Ib1.1 to Ib1.420 in that R13 is 2-adamantyl. 
Most particular preference is also given to the compounds of the formula Ib10, in particular to the compounds Ib10.1 to Ib10.420 which differ from the compounds Ib1.1 to Ib1.420 in that R13 is 2-adamantyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ib11, in particular to the compounds Ib11.1 to Ib11.420 which differ from the corresponding compounds Ib1.1 to Ib1.420 in that R1 is methyl. 
Most particular preference is also given to the compounds of the formula Ib12, in particular to the compounds Ib12.1 to Ib12.420 which differ from the corresponding compounds Ib1.1 to Ib1.420 in that R1 is methyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ib13, in particular to the compounds Ib13.1 to Ib13.420 which differ from the compounds Ib1.1 to Ib1.420 in that R1 is methyl and R13 is cyclopentyl. 
Most particular preference is also given to the compounds of the formula Ib14, in particular to the compounds Ib14.1 to Ib14.420 which differ from the compounds Ib1.1 to Ib1.420 in that R1 is methyl, R13 is cyclopentyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ib15, in particular to the compounds Ib15.1 to Ib15.420 which differ from the compounds Ib1.1 to Ib1.420 in that R1 is methyl and R13 is cyclohexyl. 
Most particular preference is also given to the compounds of the formula Ib16, in particular to the compounds Ib16.1 to Ib16.420 which differ from the compounds Ib1.1 to Ib1.420 in that R1 is methyl, R13 is cyclohexyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ib17, in particular to the compounds Ib17.1 to Ib17.420 which differ from the compounds Ib1.1 to Ib1.420 in that R1 is methyl and R13 is 2-norbornyl. 
Most particular preference is also given to the compounds of the formula Ib18, in particular to the compounds Ib18.1 to Ib18.420 which differ from the compounds Ib1.1 to Ib1.420 in that R1 is methyl, R13 is 2-norbornyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ib19, in particular to the compounds Ib19.1 to Ib19.420 which differ from the compounds Ib1.1 to Ib1.420 in that R1 is methyl and R13 is 2-adamantyl. 
Most particular preference is also given to the compounds of the formula Ib20, in particular to the compounds Ib20.1 to Ib20.420 which differ from the compounds Ib1.1 to Ib1.420 in that R1 is methyl, R13 is 2-adamantyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ib21, in particular to the compounds Ib21.1 to Ib21.420 which differ from the corresponding compounds Ib1.1 to Ib1.420 in that R1 is methoxy. 
Most particular preference is also given to the compounds of the formula Ib22, in particular to the compounds Ib22.1 to Ib22.420 which differ from the corresponding compounds Ib1.1 to Ib1.420 in that R1 is methoxy and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ib23, in particular to the compounds Ib23.1 to Ib23.420 which differ from the compounds Ib1.1 to Ib1.420 in that R1 is methoxy and R13 is cyclopentyl. 
Most particular preference is also given to the compounds of the formula Ib24, in particular to the compounds Ib24.1 to Ib24.420 which differ from the compounds Ib1.1 to Ib1.420 in that R1 is methoxy, R13 is cyclopentyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ib25, in particular to the compounds Ib25.1 to Ib25.420 which differ from the compounds Ib1.1 to Ib1.420 in that R1 is methoxy and R13 is cyclohexyl. 
Most particular preference is also given to the compounds of the formula Ib26, in particular to the compounds Ib26.1 to Ib26.420 which differ from the compounds Ib1.1 to Ib1.420 in that R1 is methoxy, R13 is cyclohexyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ib27, in particular to the compounds Ib27.1 to Ib27.420 which differ from the compounds Ib1.1 to Ib1.420 in that R1 is methoxy and R13 is 2-norbornyl. 
Most particular preference is also given to the compounds of the formula Ib28, in particular to the compounds Ib28.1 to Ib28.420 which differ from the compounds Ib1.1 to Ib1.420 in that R1 is methoxy, R13 is 2-norbornyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ib29, in particular to the compounds Ib29.1 to Ib29.420 which differ from the compounds Ib1.1 to Ib1.420 in that R1 is methoxy and R13 is 2-adamantyl. 
Most particular preference is also given to the compounds of the formula Ib30, in particular to the compounds Ib30.1 to Ib30.420 which differ from the compounds Ib1.1 to Ib1.420 in that R1 is methoxy, R13 is 2-adamantyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ic1 (=I where R1=Cl, R3 and R6 or R3 and R8 together form a bond, R13=cyclo-C3H5 and R5 and R14=H), in particular to the compounds Ic1.1-Ic1.720 of Table 3, where the radical definitions are of particular importance for the compounds according to the invention not only in combination with one another but in each case also on their own. 
Most particular preference is also given to the compounds of the formula Ic2, in particular to the compounds Ic2.1 to Ic2.720 which differ from the corresponding compounds Ic1.1 to Ic1.720 in that R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ic3, in particular to the compounds Ic3.1 to Ic3.720 which differ from the compounds Ic1.1 to Ic1.720 in that R13 is cyclopentyl. 
Most particular preference is also given to the compounds of the formula Ic4, in particular to the compounds Ic4.1 to Ic4.720 which differ from the compounds Ic1.1 to Ic1.720 in that R13 is cyclopentyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ic5, in particular to the compounds Ic5.1 to Ic5.720 which differ from the compounds Ic1.1 to Ic1.720 in that R13 is cyclohexyl. 
Most particular preference is also given to the compounds of the formula Ic6, in particular to the compounds Ic6.1 to Ic6.720 which differ from the compounds Ic1.1 to Ic1.720 in that R13 is cyclohexyl and R14 is Methyl. 
Most particular preference is also given to the compounds of the formula Ic7, in particular to the compounds Ic7.1 to Ic7.720 which differ from the compounds Ic1.1 to Ic1.720 in that R13 is 2-norbornyl. 
Most particular preference is also given to the compounds of the formula Ic8, in particular to the compounds Ic8.1 to Ic8.720 which differ from the compounds Ic1.1 to Ic1.720 in that R13 is 2-norbornyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ic9, in particular to the compounds Ic9.1 to Ic9.720 which differ from the compounds Ic1.1 to Ic1.720 in that R13 is 2-adamantyl. 
Most particular preference is also given to the compounds of the formula Ic10, in particular to the compounds Ic10.1 to Ic10.720 which differ from the compounds Ic1.1 to Ic1.720 in that R13 is 2-adamantyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ic11, in particular to the compounds Ic11.1 to Ic11.720 which differ from the corresponding compounds Ic1.1 to Ic1.720 in that R1 is methyl. 
Most particular preference is also given to the compounds of the formula Ic12, in particular to the compounds Ic12.1 to Ic12.720 which differ from the corresponding compounds Ic1.1 to Ic1.720 in that R1 is methyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ic13, in particular to the compounds Ic13.1 to Ic13.720 which differ from the compounds Ic1.1 to Ic1.720 in that R1 is methyl and R13 is cyclopentyl. 
Most particular preference is also given to the compounds of the formula Ic14, in particular to the compounds Ic14.1 to Ic14.720 which differ from the compounds Ic1.1 to Ic1.720 in that R1 is methyl, R13 is cyclopentyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ic15, in particular to the compounds Ic15.1 to Ic15.720 which differ from the compounds Ic1.1 to Ic1.720 in that R1 is methyl and R13 is cyclohexyl. 
Most particular preference is also given to the compounds of the formula Ic16, in particular to the compounds Ic16.1 to Ic16.720 which differ from the compounds Ic1.1 to Ic1.720 in that R1 is methyl, R13 is cyclohexyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ic17, in particular to the compounds Ic17.1 to Ic17.720 which differ from the compounds Ic1.1 to Ic1.720 in that R1 is methyl and R13 is 2-norbornyl. 
Most particular preference is also given to the compounds of the formula Ic18, in particular to the compounds Ic18.1 to Ic18.720 which differ from the compounds Ic1.1 to Ic1.720 in that R1 is methyl, R13 is 2-norbornyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ic19, in particular to the compounds Ic19.1 to Ic19.720 which differ from the compounds Ic1.1 to Ic1.720 in that R1 is methyl and R13 is 2-adamantyl. 
Most particular preference is also given to the compounds of the formula Ic20, in particular to the compounds Ic20.1 to Ic20.720 which differ from the compounds Ic1.1 to Ic1.720 in that R1 is methyl, R13 is 2-adamantyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ic21, in particular to the compounds Ic21.1 to Ic21.720 which differ from the corresponding compounds Ic1.1 to Ic1.720 in that R1 is methoxy. 
Most particular preference is also given to the compounds of the formula Ic22, in particular to the compounds Ic22.1 to Ic22.720 which differ from the corresponding compounds Ic1.1 to Ic1.720 in that R1 is methoxy and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ic23, in particular to the compounds Ic23.1 to Ic23.720 which differ from the compounds Ic1.1 to Ic1.720 in that R1 is methoxy and R13 is cyclopentyl. 
Most particular preferenceis also given to the compounds of the formula Ic24, in particular to the compounds Ic24.1 to Ic24.720 which differ from the compounds Ic1.1 to Ic1.720 in that R1 is methoxy, R13 is cyclopentyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ic25, in particular to the compounds Ic25.1 to Ic25.720 which differ from the compounds Ic1.1 to Ic1.720 in that R1 is methoxy and R13 is cyclohexyl. 
Most particular preference is also given to the compounds of the formula Ic26, in particular to the compounds Ic26.1 to Ic26.720 which differ from the compounds Ic1.1 to Ic1.720 in that R1 is methoxy, R13 is cyclohexyl and R14 is methyl. 
Most particular preference is also given to the compounds of the formula Ic27, in particular to the compounds Ic27.1 to Ic27.720 which differ from the compounds Ic1.1 to Ic1.720 in that R1 is methoxy and R13 is 2-norbornyl. 
Most particular preference is also given to the compounds of the formula Ic28, in particular to the compounds Ic28.1 to Ic28.720 which differ from the compounds Ic1.1 to Ic1.720 in that R1 is methoxy, R13 is 2-norbornyl and R14 is methyl. 
Most particular preference is Also given to the compounds of the formula Ic29, in particular to the compounds Ic29.1 to Ic29.720 which differ from the compounds Ic1.1 to Ic1.720 in that R1 is methoxy and R13 is 2-adamantyl. 
Most particular preference is also given to the compounds of the formula Ic30, in particular to the compounds Ic30.1 to Ic30.720 which differ from the compounds Ic1.1 to Ic1.720 in that R1 is methoxy, R13 is 2-adamantyl and R14 is methyl. 
The 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I can be obtained by various routes, for example by the processes below.
Process A
Reaction of pyrazoles of the formula II with an activated benzoic acid IIIxcex1 or a benzoic acid IIIxcex2, which is preferably activated in situ, to give the corresponding acylation product IV, followed by rearrangement, gives compounds of the formula I where R12=OH. 
L1 is a nucleophilically displaceable leaving group, such as halogen, for example bromine, chlorine, hetaryl, for example imidazolyl, pyridyl, carboxylate, for example acetate, trifluoroacetate, etc.
The activated benzoic acid can be employed directly, such as in the case of the benzoyl halides, or be generated in situ, for example using dicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic ester, 2-pyridine disulfide/triphenylphosphine, carbonyldiimidazole, etc.
It may be advantageous to carry out the acylation reaction in the presence of a base. The reactants and the auxiliary base are advantageously employed in this case in equimolar amounts. A slight excess of auxiliary base, for example from 1.2 to 1.5 molar equivalents, based on II, may be advantageous in certain cases.
Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali metal carbonates. Suitable for use as solvents are, for example, chlorinated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene, chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures of these.
If the activated carboxylic acid component used is a benzoyl halide, it may be advantageous to cool the reaction mixture to 0-10xc2x0 C. when adding this reaction partner. The mixture is subsequently stirred at 20-100xc2x0 C., preferably at 25-50xc2x0 C., until the reaction has ended. work-up is carried out in a customary manner, for example by pouring the reaction mixture into water and extracting the product of value. Solvents which are particularly suitable for this purpose are methylene chloride, diethyl ether, dimethoxyethane and ethyl acetate. The organic phase is dried and the solvent is removed, after which the crude ester can be employed for the rearrangement without any further purification.
The rearrangement of the esters to the compounds of the formula I is advantageously carried out at 20-40xc2x0 C. in a solvent and in the presence of a base and, if appropriate, using a cyano compound as catalyst.
Suitable solvents are, for example, acetonitrile, methylene chloride, 1,2-dichlorcethane, dioxane, ethyl acetate, dimethoxyethane, toluene or mixtures of these. Preferred solvents are acetonitrile and dioxane.
Suitable bases are tertiary amines, such as triethylamine or pyridine, or alkali metal carbonates, such as sodium carbonate or potassium carbonate, which are preferably employed in an equimolar amount or an up to four-fold excess, based on the ester. Preference is given to using triethylamine or alkali metal carbonates, preferably in twice the equimolar amount, based on the ester.
Suitable cyano compounds are inorganic cyanides, such as sodium cyanide and potassium cyanide, and organic cyano compounds, such as acetone cyanohydrin and trimethylsilyl cyanide. They are employed in an amount of from 1 to 50 mol percent, based on the ester. Preference is given to using acetone cyanohydrin or trimethylsilyl cyanide, for example in an amount of from 5 to 15, preferably 10, mol percent, based on the ester.
Work-up can be carried out in the manner known per se. The reaction mixture is, for example, acidified with dilute mineral acid, such as 5% strength hydrochloric acid or sulfuric acid, and extracted with an organic solvent, for example methylene chloride or ethyl acetate. The organic extract can be extracted with 5-10% strength alkali metal carbonate solution, for example sodium carbonate or potassium carbonate solution. The aqueous phase is acidified and the resulting precipitate is filtered off with suction and/or extracted with methylene chloride or ethyl acetate, and the mixture is dried and concentrated. (Examples for the preparation of esters of hydroxypyrazoles and for the rearrangement of the esters are given, for example, in EP-A 282 944 and U.S. Pat. No. 4,643,757).
However, it is also possible to generate the xe2x80x9cacylation productxe2x80x9d IV in situ by reacting a pyrazole of the formula II, or an alkali metal salt thereof with a 3-(heterocyclyl)benzene derivative of the formula V in the presence of carbon monoxide, a catalyst and a base. 
L2 is a leaving group, such as halogen, for example chlorine, bromine or iodine, or sulfonate, such as mesylate or triflate; preference is given to bromine or triflate.
The xe2x80x9cacylation productxe2x80x9d IV proceeds to react, directly or indirectly, to give the 1-cycloalkylpyrazolylbenzoyl derivative of the formula I.
Suitable catalysts are palladium-ligand complexes in which the palladium is present in oxidation state 0, metallic palladium, which has optionally been absorbed on a carrier, and preferably palladium(II) salts. The reaction with palladium(II) salts and metallic palladium is preferably carried out in the presence of complex ligands.
An example of a suitable palladium(0)-ligand complex is tetrakis(triphenylphosphine)palladium.
Metallic palladium is preferably absorbed on an inert carrier such as, for example, activated carbon, silica, alumina, barium sulfate or calcium carbonate. The reaction is preferably carried out in the presence of complex ligands such as, for example; triphenylphosphine.
Examples of suitable palladium(II) salts are palladium acetate and palladium chloride. The presence of complex ligands such as, for example, triphenylphosphine is preferred.
Suitable complex ligands for the palladium-ligand complexes, or in whose presence the reaction is preferably carried out with metallic palladium or palladium(II) salts, are tertiary phosphines whose structure is represented by the following formulae: 
where z is 1 to 4 and the radicals Ra to Rg are C1-C6-alkyl, C3-C6-cycloalkyl, aryl-C1-C2-alkyl or, preferably, aryl. Aryl is, for example, naphthyl and unsubstituted or substituted phenyl such as, for example, 2-tolyl and, in particular, unsubstituted phenyl.
The complex palladium salts can be prepared in a manner known per se starting from commercially available palladium salts such as palladium chloride or palladium acetate and the appropriate phosphines such as, for example, triphenylphosphine or 1,2-bis(diphenylphosphino)ethane. Many of the complexed palladium salts are commercially available. Preferred palladium salts are [(R)(+)2,2xe2x80x2-bis(diphenylphosphino)-1,1xe2x80x2-binaphthyl]palladium(II) chloride, bis(triphenylphosphine)palladium(II) acetate and, in particular, bis(triphenylphosphine)palladium(II) chloride.
The palladium catalyst is usually employed in a concentration of from 0.05 to 5 mol %, and preferably 1-3 mol %.
Suitable bases are tertiary amines, such as, for example, N-methylpiperidine, ethyldiisopropylamine, 1,8-bisdimethylaminonaphthalene or, in particular, triethylamine. Also suitable is alkali metal carbonate, such as sodium carbonate or potassium carbonate. However, mixtures of potassium carbonate and triethylamine are also suitable.
In general, from 2 to 4 molar equivalents, in particular 2 molar equivalents, of the alkali metal carbonate, and from 1 to 4 molar equivalents, in particular 2 molar equivalents, of the tertiary amine are employed, based on the 3-(heterocylyl)benzene derivative of the formula V.
Suitable solvents are nitriles, such as benzonitrile and acetonitrile, amides, such as dimethylformide, dimethylacetamide, tetra-C1-C4-alkylureas or N-methylpyrrolidone and, preferably, ethers, such as tetrahydrofuran and methyl tert-butyl ethers. Particular preference is given to ethers, such as 1,4-dioxane and dimethoxyethane.
Process B
Compounds of the formula I where R12=hydroxyl are obtained by reacting compounds of the formula I where R12=hydroxyl with alkylating agents, sulfonylating agents or acylating agents L3-R12a(VI) 
L3 is a nucleophilically displaceable leaving group, such as halogen, for example bromine or chlorine, acyloxy, for example acetyloxy or ethylcarbonyloxy, or alkylsulfonyloxy, for example methylsulfonyloxy or trifluoromethylsulfonyloxy.
R12a is C1-C6-alkyl, C3-C6-alkenyl, C1-C6-alkylsulfonyl, C1-C6-alkylcarbonyl, phenylsulfonyl or phenylcarbonyl, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy.
The compounds of the formula VI can be employed directly, such as, for example, in the case of the sulfonyl halides or sulfonic anhydrides, or be generated in situ, for example activated sulfonic acids (using sulfonic acid and dicyclohexylcarbonyldiimide, carbonyldiimidazole, etc.).
The starting materials are generally employed in equimolar amounts. However, it may also be advantageous to employ an excess of one or the other component.
If appropriate, it may be advantageous to carry out the reaction in the presence of a base. The reactants and the auxiliary base are advantageously employed in equimolar amounts. An excess of auxiliary base, for example from 1.5 to 3 molar equivalents, based on I, may be advantageous in certain cases.
Suitable auxiliary bases are tertiary alkylamines, such as triethylamine, pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, and alkali metal hydrides, for example sodium hydride. Preference is given to using triethylamine and pyridine.
Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride and 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene, chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran and dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures of these.
In general, the reaction temperature is in the range from 0xc2x0 C. to the boiling point of the reaction mixture.
Work-up can be carried out in the manner known per se to give the product.
The pyrazoles of the formula II used as starting materials are known or can be prepared by processes known per se (for example EP-A 240 001 and J. Prakt. Chem. 315, 383 (1973)). The activated benzoic acids IIIxcex1 and the benzoic acids IIIxcex2 are likewise known or can be prepared in the manner known per se (for example WO 96/26206). Furthermore, the 3-(heterocyclyl)benzene derivatives of the formula V are known or can be prepared in the manner known per se (PCT/EP/99/03006).